Synthesis and Solubility of 5,5-Dimethyl-2-(phenyl(phenylamino)methyl)-1,3,2-dioxaphosphinane 2-oxide in Selected Solvents between 278.15 K and 347.15 K

Abstract

A flame retardant with enhanced phosphorus−nitrogen content, 5,5-dimethyl-2-(phenyl(phenylamino)methyl)-1,3,2-dioxaphosphinane 2-oxide (DPPO), was synthesized by the reaction of 5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (DDPO) with N-benzylideneaniline. The structure of DPPO was characterized by nuclear magnetic resonance ( 1 H NMR and 31 P NMR) and Fourier transform infrared (FT-IR) spectroscopy. The thermal stability of DPPO was characterized by thermogravimetric analysis (TGA). The solubilities of DPPO were measured in different solvents including ethyl acetate, methanol, chloroform, acetonitrile, acetone, 1,2dichloroethane, 1,4-dioxane, dichloromethane, tetrachloromethane, benzene, tetrahydrofuran, and isopropanol at temperature ranging from 278.15 to 347.15 K by the gravimetrical method. The mole fraction solubilities of DPPO in the above-mentioned organic solvents were correlated as the Apelblat equation, and the calculated values with equations shows good consistency with the experimental values. The root-mean-square deviation was less than 0.1%, and the average relative error was less than 0.04 in all of the experiments.

Solubility Determination and Data Correlation of a New Flame Retardant 3,9-Bis(phenyl(phenylamino)methyl)-2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane 3,9-dioxide in 12 Pure Solvents from 283.15 to 343.15 K

“…BTDD solubility is affected by a variety of factors, such as molecule structure, dielectric constant (ε), the solubility parameters (δ), the rule of "like dissolves like", the hydrogen bond, and so on. 19 To be specific, BTDD is more likely to form hydrogen bonds with tetrahydrofuran; therefore, BTDD shows the highest solubility in tetrahydrofuran. BTDD is more likely to dissolve in toluene with less polarity, and this may be due to the highly symmetrical structure of BTDD, which leads to its low polarity.…”

“…At temperatures ranging from 283.15 to 310.15 K, it ranks as dichloromethane > 1,2-dichloroethane > isopropanol > (diethyl ether, 1,4-dioxane) > acetic acid > acetone > benzene > (ethanol, acetonitrile). BTDD solubility is affected by a variety of factors, such as molecule structure, dielectric constant (ε), the solubility parameters (δ), the rule of “like dissolves like”, the hydrogen bond, and so on . To be specific, BTDD is more likely to form hydrogen bonds with tetrahydrofuran; therefore, BTDD shows the highest solubility in tetrahydrofuran.…”

“…The melting point of DHDP is 408. NDPA 19 and 10 mL of acetonitrile solution were added. Then, 2.97 g (0.01 mol) of DHDP was preheated, dissolved in 10 mL of acetonitrile, and added dropwise to the reaction system, and the temperature was raised to 323.15 K. The reaction was carried out for 5 h and then cooled to room temperature.…”

“…BTDD was synthesized by the P–H group reaction with the amidogen group of Schiff base forming a P–C bond via nucleophilic addition. In a 50 mL three-necked flask, 3.42 g (0.02 mol) of Schiff base (2-( N -phenyliminomethyl)­phenol) NDPA and 10 mL of acetonitrile solution were added. Then, 2.97 g (0.01 mol) of DHDP was preheated, dissolved in 10 mL of acetonitrile, and added dropwise to the reaction system, and the temperature was raised to 323.15 K. The reaction was carried out for 5 h and then cooled to room temperature.…”

Thermodynamic Modeling, Hansen Solubility Parameters, and Solubility Behavior of N-Benzyloxycarbonyl-l-asparagine in Twelve Pure Solvent Systems at 283.15–323.15 K

“…In the industry purification process, recrystallization from solutions is an important unit operation whose development and design heavily rely on the equilibrium solubility data which normally vary with temperatures and solution compositions. , With accurate solubility data, optimal crystallizer configurations and operation conditions together with the selection of the solvent for a specific solute can be achieved. In addition, solubility has a great influence on the crystallization characteristics of the products, such as the yield, purity, polycrystalline structure, and grain size distribution. , As the basis of the crystallization process, the solubility of N -benzyloxycarbonyl- l -asparagine has not been reported previously.…”